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250376

Sigma-Aldrich

4-Formylmorpholine

99%

Synonym(s):

4-Morpholinecarboxaldehyde

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About This Item

Empirical Formula (Hill Notation):
C5H9NO2
CAS Number:
4394-85-8
Molecular Weight:
115.13
Beilstein:
110293
EC Number:
224-518-3
MDL number:
MFCD00006170
UNSPSC Code:
12352100
PubChem Substance ID:
24855051
NACRES:
NA.22

Quality Level

200

Assay

99%

form

solid

refractive index

n20/D 1.485 (lit.)

bp

236-237 °C (lit.)

mp

20-23 °C (lit.)

density

1.145 g/mL at 25 °C (lit.)

SMILES string

[H]C(=O)N1CCOCC1

InChI

1S/C5H9NO2/c7-5-6-1-3-8-4-2-6/h5H,1-4H2

InChI key

LCEDQNDDFOCWGG-UHFFFAOYSA-N

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General description

Treatment of 4-formylmorpholine with sulphur tetrafluoride in the presence of potassium fluoride gives 4-(trifluoromethyl)morpholine in excellent yields. 4-Formylmorpholine reacts with series of 2-alkyl-2-cyclohexen-1-ones in the presence of POCl3 to give the corresponding 3-alkyl-2-chloro-5,6-dihydrobenzaldehydes and allylic alcohols (by-product).

Application

4-Formylmorpholine has been used in the preparation of:
  • adenine hydrochloride labelled with 14C
  • terphenyl dialdehyde

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

244.4 °F - DIN 51758

Flash Point(C)

118 °C - DIN 51758

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Cyclic host having double bonds as bridging units.
Paek K-S and Cram DJ.
Bull. Korean Chem. Soc., 10(6), 569-569 (1989)
Studies in vilsmeier chemistry, V. Vilsmeier reactions of 2-alkyl-2-cyclohexen-1-ones: A novel route to dihydrobenzaldehydes, the formation of allyl alcohols as by-products, and the X-ray crystallographic structure of 3-chloro-2-methyl-2-cyclohexen-1-ol.
Katritzky AR, et al.
Chemische Berichte, 121(5), 999-1003 (1988)
209. A synthesis of adenine labelled with 14C.
Clark VM and Kalckar HM.
Journal of the Chemical Society, 1029-1030 (1950)
Reaction of tertiary formamides with sulphur tetrafluoride. Direct synthesis of (trifluoromethyl) amines.
Dmowski W and Kaminski M.
Journal of Fluorine Chemistry, 23(3), 207-218 (1983)

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